How To Be A Master At Starting Conversation

how to be a master at starting conversation

Awkwardness often comes in the form of approaching a girl and attempting conversation.

I can remember too many times when I wanted to approach a girl at church, and decided I would after I got back in the donut and coffee line. Maybe you see the girl you want to talk to at a bar, and you make a resolution you will after one more drink. Or perhaps you see her in a social setting, and resolve to do it after talking to a few more people.

Get over the fear of starting conversation

I can’t begin to tell you how much making the career jump to sales has helped me be a master at starting conversation. It’s what I’m paid to do. But I can remember the fear of striking out on my own. When I pulled up to that very first office in the little town of Mountain Grove, MO all on my own, I was terrified. That first sales call was mediocre at best, but you know what? Dr. Hill and his staff became some of my favorite clientele. They started coming to all of my programs. He started inviting me to his parties.

The point is, when you begin your endeavor to become a master at starting conversation, realize it’s not a sprint, but a marathon. It’s okay to lose the first hundred meters, the second hundred meters, etc. Your goal is to win the race.

How to be a master at conversation.

First, practice and start conversation. The best moments to practice this trade are when you are waiting…for a coffee, at the DMV, at the store, on transportation. If you improve how you interact with people in general, then starting a conversation with a girl who catches your eye can be a breeze.

Well, almost.

Get over yourself

I distinctly remember when I became a pharmaceutical rep. I walked into an office and found myself waiting next to this bombshell of a rep from another company. I confidently introduced myself, and asked her all of the standard run-of-the-mill questions: how long had she worked in the industry, where she went to college, etc.

It turns out she went to the same college as me, and commonality is a good thing. But then the conversation went south. I attempted to impress her.

When did you graduate? Ah, that was the year I won Homecoming King. Were you involved on campus? I was inducted into the Student Involvement Hall of Fame. 


The moment you feel the need to justify yourself is the moment you have lost. If you find yourself discussing who you know, what you do, what kind of car you have, where you live…she doesn’t care. People care about themselves.

Get her to talk

One way to avoid bragging, which is always a turn-off, is to keep the attention focused on her. Ask her open-ended questions (such as what, how, and why) vs. questions that only require “yes” or “no” responses.

As a sales professional, I’m always attempting to keep dialogue moving, so I’ll ask questions or ask an opinion on a topic even if I already know about it.

As an example, even if you are a coffee connoisseur, you can ask someone in line at the coffee shop about how they order theirs. Everyone loves to share their opinion on something they are passionate about.

I observed this guy who’s a pro at starting conversations…a tad too pushy, though. We were leaving dinner with my sister-in-law, and she’s very beautiful, so she commands attention. This guy starts throwing out a ton of open-ended questions, asking our opinions on random movies. Though we were dead-set on leaving and Kenzie wasn’t interested in him at all, we found ourselves stuck in this vortex of questioning. We finally got away 8 minutes later! Even though the girls were super annoyed, I was amazed how he got us to talk to him that long.

His questioning was on point, but his timing was way off.

Timing and paying attention to non-verbal signs

Once again, it’s important to remember starting conversations is a marathon, not a race. In my sales calls, if I walk into a doctor’s office and it’s clear the doctor is super busy, stressed, and has no interest in talking to me, I recognize it, and find a time to come back that will work better. In the same way, pay attention to her non-verbal language.

If you’re seeing her for the first time, keep in mind, you approached her because of her looks and she’s probably going to respond based on yours. The good news is, if attractiveness is not on your side, then time can be. It takes time and intention to get to know someone’s heart. A perfect 10 can easily become a 6 if the heart isn’t attractive, but a 6 can become a 10 when the heart is solid.

Don’t try too hard, and don’t be desperate. If you find yourself falling into these patterns, take a step back. When you approach her for conversation with strong inner strength, favor is likelier to follow you.

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3 Responses to How To Be A Master At Starting Conversation

  1. Gabe June 19, 2015 at 6:31 pm #

    I bless the day when I found this site. It is totally changed my life and guide me into a better future. I’m lucky that I found it in such an early age(I’m 18), it saves me from a lot of bad decisions I’d make. I was anxious, depressed my life was going so bad, but now I can see the light.You even restored and streghtened my faith in God. can’t tell how thankful I am for your works guys here at the goodguyswag.

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    • Kris Wolfe July 8, 2015 at 6:20 pm #

      Messages like this are what I live for Gabe, so thank you brother I apologize I’m a little bit behind on replying back to your comments.

  2. Clint June 29, 2016 at 6:18 pm #


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